- Pi-conjugated chain extenders for the synthesis of optoelectronic segmented polyurethanes
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The optical properties of mechanochromic materials change under mechanical stress. Segmented polyurethanes are elastomers composed of amorphous, saturated chain soft segments, and rigid pi-conjugated hard domains. Within aggregates of hard domains pi-pi interactions may form and result in perturbation of the optoelectronic properties of the system. Disruption and restoration of these electronic interactions within the material may lead to observable mechanochromic response. A series of oligothiophene diols and diamines, as well as a naphthalene diimide diol, have been synthesized for incorporation into the hard domains of segmented polyurethanes and polyureas using long poly(tetramethylene oxide) chains as soft segments. The resulting polymers were evaluated to determine their extent of polymerization and their thermal stability. The optical properties of the materials were studied in solution and as thin films. Where possible the electrochemical properties of the polymers were also explored. The length of the soft segment chains in the segmented polyurethanes hindered electronic coupling of hard domains. Future work involving smaller, more solubilizing soft segments may allow for easier material characterization and mechanochromic response.
- Harvey, Christopher P.,Tovar, John D.
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Read Online
- Identification of Pyrazolo[1,5- a]pyridine-3-carboxamide Diaryl Derivatives as Drug Resistant Antituberculosis Agents
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A series of pyrazolo[1,5-a]pyridine-3-carboxamide (PPA) derivatives bearing diaryl side chain was designed and synthesized as new antituberculosis agents, aiming to improve the efficacy toward drug resistant Mycobacterium tuberculosis (Mtb) strains. Most
- Hu, Xianglong,Wan, Baojie,Liu, Yang,Shen, Jiayi,Franzblau, Scott G.,Zhang, Tianyu,Ding, Ke,Lu, Xiaoyun
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Read Online
- Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines
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Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.
- Ingale, Ajit P.,Garad, Dnyaneshwar N.,Ukale, Dattatraya,Thorat, Nitin M.,Shinde, Sandeep V.
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supporting information
p. 3791 - 3804
(2021/11/04)
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- Tuning the sensitivity towards mercury: Via cooperative binding to d-fructose: Dual fluorescent chemosensor based on 1,8-naphthyridine-boronic acid derivative
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A novel fluorescent chemosensor naphthyridine-boronic acid derivative (1.1) was synthesized and its ability to act as a selective chemosensor was examined for various metal ions. Compound 1.1 displayed highly selective fluorescence quenching upon interaction with Hg2+, possibly by means of photo induced electron transfer (PET) mechanism. The binding stoichiometry of the naphthyridine-boronic acid-Hg2+ complex and the association constant was determined. It was found that in the presence of d-fructose at physiological concentration, the sensitivity of chemosensor 1.1 towards Hg2+ improved by at least 7 times, perhaps as a result of the cooperative binding of both d-fructose and mercury ion to the sensor. Till now, the presented dual d-fructose-mercury chemosensor is the first example of utilizing boronic acid-diol complexation for enhancement of the sensor's sensitivity towards a toxic metal ion. The utility of compound 1.1 lays in applications in the food industry, e.g. for detection of mercury contamination of high fructose corn syrup, or in estimation of mercury in polluted biological samples and underground water. This journal is
- Rajadurai, Marina,Reddy, E. Ramanjaneya
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p. 14862 - 14870
(2021/05/19)
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- Highly efficient chemoselective N-tert butoxycarbonylation of aliphatic/aromatic/heterocyclic amines using diphenylglycoluril as organocatalyst
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An efficient approach for the Chemoselective N-tert-butoxycarbonylation of a variety of amines using diphenylglycoluril as organocatalyst has been described. For the first time, a plausible mechanism for the N-tert-butoxycarbonylation has been proposed using density functional theory (DFT) calculations supported by NMR studies. The reusability of the organocatalyst and observation of the desired N-Boc protected amines being formed without the formation of side products like urea, oxazolidinone, isocyanate, and N, N-di-Boc derivatives makes the present protocol desirable.
- Awasthi, Amardeep,Mukherjee, Anagh,Singh, Mandeep,Rathee, Garima,Vanka, Kumar,Chandra, Ramesh
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- Novel quinazoline EGFR inhibitor, and preparation method and application thereof
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A novel quinazoline EGFR inhibitor, and a preparation and an application thereof belong to the field of synthesis of medicines. The novel quinazoline EGFR inhibitor has a general formula shown in thedescription; and in the general formula, R is one from H, F, Cl, Br, and I, and R1 and R2 are same to or different from each other, and are respectively selected from H, a nitro group, an amino group,a hydroxyl group, a 2-methoxyethoxy group, a C1-C4 alkoxy group and a C1-C4 alkyl group. The novel quinazoline EGFR inhibitor is different from existing quinazoline inhibitors with the 4-position substituted with various anilines, and is designed and synthesized by substituting the 4-position of a quinazoline skeleton with a broadly bioactive thienylmethylamine and reasonably modifying the 6-position and the 7-position with groups not including an electrophilic acrylamide bond in order to avoid covalent bonds with EGFR. Compared with existing antitumor drugs, the above compound can significantly inhibit EGFR phosphorylation, and has excellent anti-proliferative activity against EGFR overexpressing tumor cells (such as A431 and MCF-7).
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Paragraph 0026
(2019/10/01)
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- COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN
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Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting of N6-[(3-halothien-2-yl)methyl]adenosine, N6-[(4-halothien-2-yl)methyl]adenosine, and N6-[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting of N6-[(2-bromothien-3-yl)methyl]adenosine, N6-[(4-bromothien-3-yl)methyl]adenosine, N6-[(5-bromothien-3-yl)methyl]adenosine N6-[(2-chlorothien-3-yl)methyl]adenosine, N6-[(4-chlorothien-3-yl)methyl]adenosine, and N6-[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.
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Paragraph 0040; 0059
(2020/09/17)
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- Synthesis and biological evaluation of some novel thiophene-bearing quinazoline derivatives as EGFR inhibitors
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Background: With the approval of gefitinib, erlotinib, afatinib, and osimertinib for clinical use, targeting Epidermal Growth Factor Receptor (EGFR) has been intensively pursued. Similar to most therapies, challenges related to the treatment resistance against these drugs have emerged over time, so new EGFR Tyrosine Kinase Inhibitors (TKIs) need to be developed. This study aimed to investigate the potential use of a series of thiophene-bearing quinazoline derivatives as EGFR inhibitors. We designed and synthesized nine quinazolin derivatives, among which five compounds (5e, 5f, 5g, 5h, and 5i) were reported for the first time. Methods: Two cancer cell lines, A431 (overexpressing EGFR) and A549 (EGFR wild-type and K-ras mutation), were treated by these compounds and subjected to MTT assay. The A431 cells were selected for further treatment (5e) and Western blot analysis. Results: Although the compounds exerted no obvious effects on the proliferation of A549 cells, seven out of the nine compounds significantly inhibited the growth of A431 cells. In particular, the IC50 values of 5e and erlotinib were nearly equal. Western blot results showed that 5e significantly inhibited EGFR autophosphorylation in A431 cells. Structure-activity relationships indicated that quinazolines bearing 6,7-side chains were more potent than those unsubstituted at the 6,7-positions. Moreover, electron-withdrawing hydrophobic groups on the 5-position of the thiophene were preferred, such as chlorine or bromine atom. Conclusion: Nine 4-aminoquinazolin derivatives were designed, synthesized, and evaluated against A431 and A549 cell lines. Seven compounds significantly inhibited the growth of A431 cells. In particular, 5e possessed similar antitumor potency to that of erlotinib.
- Zou, Min,Jin, Bo,Liu, Yanrong,Chen, Huiping,Zhang, Zhuangli,Zhang, Changzheng,Zhao, Zhihong,Zheng, Liyun
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p. 102 - 110
(2019/01/04)
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- COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN
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Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting ofN 6 -[(3-halothien-2-yl)methyl]adenosine,N 6 -[(4-halothien-2-yl)methyl]adenosine, andN 6 -[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting ofN 6 -[(2-bromothien-3-yl)methyl]adenosine,N 6 -[(4-bromothien-3-yl)methyl]adenosine,N 6 -[(5-bromothien-3-yl)methyl]adenosineN 6 -[(2-chlorothien-3-yl)methyl]adenosine,N 6 -[(4-chlorothien-3-yl)methyl]adenosine, andN 6 -[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.
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Paragraph 0040; 0059
(2019/01/06)
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- Pyrazolo[1, 5-a]pyridine compound and use thereof
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The invention discloses a pyrazolo[1, 5-a]pyridine compound with the structure characteristic shown in the formula (I) or its pharmaceutically acceptable salt, stereoisomer or prodrug molecule and a use thereof. The compound has good in-vitro anti-tubercle bacillus activity, has the minimal inhibitory concentration (MIC) less than 0.1 micrograms per milliliter and partial MIC of 0.01 micrograms per milliliter and has strong inhibition effects on a clinically sorted multi-drug-resistant tuberculosis (MDR-TB) strain. In an in-vivo experiment, at a dosage of 20mg/kg/d, the pyrazolo[1, 5-a]pyridine compound can effectively eliminate H37Ra infection in a mouse and is a novel anti-tuberculosis compound.
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Paragraph 0363; 0364; 0365; 0366; 0367
(2016/10/08)
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- A thiazole-containing compounds of structure, its preparation and use
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The invention relates to the field of drugs related to diabetes, and particularly relates to a compound containing a thiazole structure, a preparation method of the compound, a drug composite containing the compound and application of the compound in preparation of a diabetes drug. R is C1-C5 alkyl, preferably, Me.
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Paragraph 0037; 0038
(2016/11/14)
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- COMPOUNDS FOR USE IN PREVENTION AND TREATMENT OF NEURODEGENERATIVE DISEASES AND PAIN
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Compounds for use in prevention and treatment of neurodegenerative disease and pain are disclosed. In one embodiment of the invention, the compound is selected from the group consisting of N66-[(3-halothien-2-yl)methyl]adenosine, N66-[(4-halothien-2-yl)methyl]adenosine, and N66-[(5-halothien-2-yl)methyl]adenosine. In another embodiment of the invention, the compound is selected from the group consisting of N66-[(2-bromothien-3-yl)methyl]adenosine, N66-[(4-bromothien-3-yl)methyl]adenosine, N66-[(5-bromothien-3-yl)methyl]adenosine N66-[(2-chlorothien-3-yl)methyl]adenosine, N66-[(4-chlorothien-3-yl)methyl]adenosine, and N66-[(5-chlorothien-3-yl)methyl]adenosine. Also disclosed are methods of making and using the same.
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Page/Page column 15; 16
(2015/05/06)
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- Rapid assessment of protecting-group stability by using a robustness screen
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An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions. Assessment of up to twelve protecting groups in a single experiment has been demonstrated. Evaluation of this protocol in two unrelated synthetic transformations suggests that this method can be used to select appropriate protecting groups in the design of synthetic routes.
- Collins, Karl D.,Ruehling, Andreas,Lied, Fabian,Glorius, Frank
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supporting information
p. 3800 - 3805
(2014/04/03)
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- HETEROCYCLIC AMIDE DERIVATIVE AND PHARMACEUTICAL PRODUCT CONTAINING SAME
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The present invention aims to provide a novel compound having a TRPA1 antagonist activity, and a medicament containing the compound. Moreover, the present invention aims to provide a TRPA1 antagonist and a medicament useful for the prophylaxis or treatmen
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Paragraph 0318
(2014/11/13)
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- NOVEL 2-PIPERIDIN-1-YL-ACETAMIDE COMPOUNDS FOR USE AS TANKYRASE INHIBITORS
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The present invention provides for compounds of formula (I), wherein R1-R5 and L are defined herein. The present invention also provides for pharmaceutical compositions and combinations comprising a compound of formula (I) as well as for the use of such compounds as tankyrase inhibitors and in the treatment of Wnt signaling and tankyrase 1 and 2 signaling related disorders which include, but are not limited to, cancer.
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Page/Page column 49
(2013/03/26)
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- An efficient labeling strategy of drug like molecules with functionalized alkyl linkers using CH-activation
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Heterocyclic drugs can be cross-coupled with functionalized thiophene derivatives under dehydrogenative conditions using Pd-catalysts. Upon reductive desulfurization an alkyl linker is introduced with a functional group at its terminus, which will allow the immobilization of the drug molecule onto a solid support for chemical proteomics.
- Rentner, Jana,Breinbauer, Rolf
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supporting information
p. 10343 - 10345
(2012/11/07)
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- One-pot synthesis of α-amino acids from imines through CO2 incorporation: An alternative method for strecker synthesis
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Itas a gas: A novel one-pot process for the synthesis of α-amino acids from imine equivalents using CO2 gas as a carbon source has been developed. This reaction was made possible by the reagent combination of TMSSnBu3 and CsF (see scheme). Three successive reactions (imine formation, stannylation, and carboxylation) proceeded in the same flask under these conditions to give products in up to 79 % yield. Boc=tert-butoxycarbonyl, TMS=trimethylsilyl.
- Mita, Tsuyoshi,Chen, Jianyang,Sugawara, Masumi,Sato, Yoshihiro
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p. 1393 - 1396
(2011/04/22)
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- Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides
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Potassium Boc-protected aminomethyltrifluoroborate, a primary aminomethyl equivalent, was synthesized successfully through a "one-pot" process. With this trifluoroborate, Suzuki-Miyaura cross-coupling reactions were investigated with a variety of both aryl and hetaryl chlorides in good to excellent yields.
- Molander, Gary A.,Shin, Inji
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p. 3956 - 3959
(2011/10/03)
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- Palladium-catalysed direct 5-arylation of furfurylamine or 2-(aminoalkyl)-thiophene derivatives
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The palladium-catalysed direct 5-arylation of furan or thiophene derivatives bearing CH2NHR substituents (with. R = COMe or CO 2tBu) generally proceeds in good yields by using a catalysts loading of only 0.1-2 mol-%. A wide range of functions such as acetyl, propionyl, formyl, ester, nitrile, trifluoromethyl or fluoro on the aryl bromide is tolerated. Higher yields were generally obtained in the presence of electron-deficient aryl bromides than with, electron-rich aryl bromides.
- Roger, Julien,Doucet, Henri
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experimental part
p. 4412 - 4425
(2010/10/19)
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- Assembling p-type molecules on single wall carbon nanotubes for photovoltaic devices
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We report the design and synthesis of an oligothiophene molecule that noncovalently functionalizes carbon nanotubes to create a hybrid material for photovoltaic devices.
- Klare, Jennifer E.,Murray, Ian P.,Goldberger, Joshua,Stupp, Samuel I.
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supporting information; experimental part
p. 3705 - 3707
(2009/12/01)
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- PYRIDINONYL PDK1 INHIBITORS
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The present invention provides pyridinonyl PDKl inhibitors and methods of treating cancer using the same.
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Page/Page column 185
(2008/06/13)
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